Nanohybrid catalyst for hydrogenation reactions

Abstract

A nanohybrid material includes a plurality of gold nanohybrid particles having formula (I). The gold nanohybrid particles have a gold nanoparticle (AuNPs) core and a shell of at least one fatty acid derivative at least partially disposed around the AuNPs core. The AuNPs core has a cuboidal shape and an average particle size of 20 to 60 nanometers (nm). Each R 1 , and R 2 are independently selected from the group consisting of a hydrgon atom, and a fatty acid hydrocarbon chain having 16 to 22 carbon atoms. R 3 is selected from the group consisting of a hydrogen atom, an alkyl, an alkoxy, an optionally substituted alkoxy having 1 to 10 carbon atoms, and an optionally substituted alkoxyalky.

1 : A nanohybrid material, comprising:
 a plurality of gold nanohybrid particles having formula (I);   wherein the gold nanohybrid particles have a gold nanoparticle (AuNPs) core and a shell of at least one fatty acid derivative at least partially disposed around the AuNPs core;   wherein the AuNPs core has a cuboidal shape and an average particle size of 20 to 60 nanometers (nm);   wherein formula (I) is   
       
         
           
           
               
               
           
         
         wherein each R 1 , and R 2  are independently selected from the group consisting of a hydrgon atom, and a fatty acid hydrocarbon chain having 16 to 22 carbon atoms; 
         wherein R 3  is selected from the group consisting of a hydrogen atom, an alkyl, an alkoxy, an optionally substituted alkoxy having 1 to 10 carbon atoms, and an optionally substituted alkoxyalky; and 
         n is any positive integer. 
       
     
     
         2 : The nanohybrid material of  claim 1 , having a multi-layered porous structure. 
     
     
         3 : The nanohybrid material of  claim 2 , wherein the multi-layered porous structure of the nanohybrid material has an average layer thickness of 60 to 500 nm. 
     
     
         4 : The nanohybrid material of  claim 1 , having a pore size of 1 to 20 micrometers (μm). 
     
     
         5 : The nanohybrid material of  claim 1 , wherein a weight ratio of the AuNPs core to the fatty acid derivative shell in the nanohybrid material ranges from about 1:10 to 1:50. 
     
     
         6 : The nanohybrid material of  claim 1 , wherein the AuNPs core comprises Au nanoparticles having a plurality of carboxylate functional groups, wherein the at least one fatty acid derivative is connected to a carboxylate functional group of the plurality of carboxylate functional groups of the Au nanoparticles. 
     
     
         7 : The nanohybrid material of  claim 1 , wherein the gold nanohybrid particles are uniformly distributed throughout the nanohybrid material and not forming aggregates. 
     
     
         8 : The nanohybrid material of  claim 1 , wherein the gold nanohybrid particle is (9Z,9′Z,9″Z,12Z,12′Z,12″Z)-5-((2-hydroxyethoxy)carbonyl)benzene-1,2,3-triyl tris(octadeca-9,12-dienoate) (AuNPs/HCBTDE) having formula (II) 
       
         
           
           
               
               
           
         
         and n is any positive integer. 
       
     
     
         9 : A method of making the nanohybrid material of  claim 8 , comprising:
 mixing and dissolving at least one fatty acid derivative having formula (III) in a first solvent to form a surfactant solution;   drop-wise adding the surfactant solution into a dispersion containing the AuNPs under continuous agitation to from a reaction mixture containing the nanohybrid material; and   drying the reaction mixture to from the nanohybrid material;   wherein formula (III) is   
       
         
           
           
               
               
           
         
       
     
     
         10 : The method of  claim 9 , wherein a volume ratio of the surfactant solution to the dispersion is in a range of 1:2 to 1:10. 
     
     
         11 : The method of  claim 9 , wherein the AuNPs present in the dispersion have an average particle size of 30 to 50 nm. 
     
     
         12 : The method of  claim 9 , further comprising:
 preparing the at least one fatty acid derivative of formula (III) by:   mixing a fatty acid and a trihydroxybenzoic acid in a second solvent in the presence of a sulfonic acid and refluxing to form a first product having formula (IV);   
       
         
           
           
               
               
           
         
         mixing the first product and ethylene glycol in the second solvent in the presence of a sulfonic acid and refluxing to form the at least one fatty acid derivative having formula (III). 
       
     
     
         13 : The method of  claim 12 , wherein a molar ratio of the fatty acid to the trihydroxybenzoic acid is in a range of 2:1 to 1:2. 
     
     
         14 : The method of  claim 12 , wherein a molar ratio of the first product to the ethylene glycol is in a range of 2:1 to 1:2. 
     
     
         15 : The method of  claim 12 , wherein the fatty acid is octadeca-9,12-dienoic acid. 
     
     
         16 : The method of  claim 12 , wherein the second solvent is xylene, and wherein the sulfonic acid is p-toluene sulfonic acid. 
     
     
         17 : A method of benzaldehyde hydrogenation, comprising:
 mixing and heating an aromatic aldehyde compound, and the nanohybrid material of  claim 1  under a hydrogen flow thereby reducing the aromatic aldehyde compound with hydrogen molecules to form a reduction product;   wherein the reduction product is at least one selected from the group consisting of a substituted aromatic alcohol derivative, a substituted aromatic derivative, and an arene.   
     
     
         18 : The method of  claim 17 , wherein up to 80 wt. % of the aromatic aldehyde compound is reduced to form the reduction product at a temperature of 100 to 200° C., each wt. % based on an initial weight of the aromatic aldehyde compound. 
     
     
         19 : The method of  claim 17 , wherein a weight ratio of the nanohybrid material to the aromatic aldehyde compound is in a range of 1:200 to 1:10.